Wynn

It seems somewhere along the way I lost the draft of this little story. So I had to start over. I hope I can recreate it. And as normal I try to let your mind fill in the blow by blow details.

Wynn

Her first trip up north and another first

Part 1

I work in an office with a mixture of men and women. Everyone seems to get along real well. On Friday nights after work many of us stop for a burger and beer at a place close to the office. The group varies, on rare occasions everyone is there; many times maybe 60 to 70 percent will make it. I always stop. Being single I don't have anyone waiting for me, so I hang out to the end.

As can be expected more than half our staff are female and most of them are young. Being in my mid-fifties I really enjoy the mind candy. That's the main reason I work. My parents have passed away but I was left with a sizable inheritance. Cash, stocks and bonds, if I wanted I could live comfortably without working.

I mentioned that I often hang around to the end of the group get together. After everyone from work has left, I might if the mood strikes me check out the ladies that are around and alone and if I chat up one and she is agreeable spend some quality time with her. I make no excuses about my conduct and I am upfront with my plans. I am single and I intend to stay that way. My affairs with the gentle sex are short. Sometimes it's a month or a week or two, maybe only several nights. One night stands sometimes. It is surprising how many ladies have the same feelings about it as I do.

On a boring Saturday I was surfing the web and ran across an article about waterfalls along the Minnesota coast and Lake Superior. After digging into it deeper the thought came to me that I should take a few days and try to photograph some of them. And it seemed that in the spring when they were running full with the spring melt would be a good time. On a Friday night I mentioned it to the group as we were drinking beer. It brought out a few questions and then the conversation moved on to other topics.             

Part 2

The middle of the following week Wynn, one of my co-workers, stopped by my cube and asked if we might talk sometime after work. We made plans to get together after work the next Wednesday and at a small Italian place across town. As we shared a pizza the questions started.

Wynn: "I've been taking an online photography class. When you mentioned the waterfalls and going up to look at them I thought that maybe I could go with you. If you thought that might be ok?"

Me: "I don't know how that would work out. I've got a small RV that I travel in."

Wynn: "I know that. You've mentioned it a couple of times on Friday nights."

Me: "It only has one bed. And it would lead to some adult activities if we were you to go with me what your Henry would think about that."

Wynn: "My Henry has left. He moved to California to get his masters in modern history."

Me: "And you would be ok with what would take place?"

Wynn: "Can I be honest?"

Me: "That would be good."

Wynn: "Ok...I know your reputation. A new woman every time you turn around. And that's how I feel. I'm not interested in having a husband and a couple of kids with a picket fence around the yard."

Me: "Whoa...everyone knows about my style?"

Wynn: "Ya, I think so."

Me: "Damn."

Wynn: "There is one more little thing I have to share."

Me: "Ok."

Wynn: "You have to promise not to tell anyone. Promise me?"

Me: "I promise."

A very long pause as she hung her head.

Wynn: "This is not easy but I'll try. You promise to keep this just between you and me, right?"

Me: "I do."

Another very long pause before she looked at me.

Wynn: "No...I can't go there. Let's just forget the whole thing. Thank you for the pizza and beer. I'll see you tomorrow at work. Let's just forget the whole thing."

Wynn got up and was out the door without looking back. I figured the conversation and her going north with me was over. To my regret, Wynn was a wonderful woman, so very good looking, with short dark hair, almost as tall as my six feet, slim, long legs, a great butt and small breasts. I expected with her personality she would be a lot of fun in the bedroom. Ah well, I would just have to go to Minnesota alone.

Part 3

Wynn avoided me the rest of the week. At the bar the next Friday night she made sure to sit as far away from me as possible. And then as the get together broke up she headed for the ladies room and reappeared after everyone else had left. I wasn't looking for any company that night so I was just finishing off my beer as she came to the table.

Me: "Hay, I thought everyone was gone. Want another beer?"

Wynn: "Maybe another one."

I signaled the waitress for a couple of beers and we sat there not saying a word until after the beers showed up.

Wynn: "Can I change my mind?"

Me: "About?"

Wynn: "Going with you to look at the waterfalls?"

Me: "Ok but let me share some information with you first."

Wynn nodded her head for me to go ahead.

Me: "I snore."

Wynn: "My dad is so loud we can hear him all through the house."

Me: "I talk in my sleep."

Wynn: "Anything interesting?"

Me: "I fart."

Wynn: "Me to."

Me: "I'm a terrible cook."

Wynn: "I can handle that. I'll bring groceries and I'll pay for the gas if you'll supply the beer."

Me: "What about the other thing?"

Wynn: "Sex?"

Me: "Yes that little thing. If I have a beautiful woman in my bed things are going to take place. And it sounded like that was off the table. To be honest that is kind of a deal breaker. Even if you a great cook and buy the gas. I'm sorry but that's kind of where it is. Can we forget the whole thing and just be friends?"

Wynn turned a deep red but still looked me right in the eyes.

Wynn: "Ok here's the whole sordid story. My Henry and I never had intercourse. I'm a virgin. "

Me: "I didn't see that coming. I mean, you've been with your boyfriend Henry for a long time as I understand. Hasn't stuff taken place? There must be something. Come on...you guys were together for ages. You never-ever did it?"

Wynn: "No never. We would do other stuff ya know. Ok...Crap. Ok...it's kind of this way. We would take care of each other by other ways. I guess I should just lay it out, ok?"

I just looked at her waiting for more information.

Wynn: "Ya want details? OK. I would put his thing in my mouth and take care of him that way."

Me: "Fellatio."

Wynn: "What?"

Me: "Fellatio, its oral sex, when someone sucks on a man's pecker."

Wynn: "Damn ten dollar words. And he would put his head between my legs and do stuff to me."

Me: "Cunnilingus."

Wynn: "If you say so. So what I'm trying to ask is...Would you be happy with just that? I've never gone all the way...With the other thing."

Me: "Never uh, maybe a finger?"

Wynn: "I bought a pretend penis and."

Me: "A Dildo. A pretend pecker, it's called a dildo."

Wynn: "Let me finish will you? I tried it and it hurt. So I threw it in the drawer and there it lies. I'm not a big fan of pain."

Me: "You apparently are not familiar with the fact the first time can be uncomfortable. Let me assure you, with time and patience and care the second time can be much more enjoyable."

Wynn: "You just want to do it to me."

Me: "You're right. I want to fuck you. I want to feel your lips around my cock and draining my balls. I want to lick your pussy until you have an orgasm and then do it until you have another one and maybe go for a third. You're beautiful and I'm a man. That's what we want to do with beautiful women."

Wynn: "Wow...You sure have a way with words don't you?"

Me: "And I promise...if you don't find it enjoyable when I poke you we'll stop for a bit before we try it again. But make no mistake...I will fuck you. And more than one time."

Wynn: "Can I please think about this? It all sounds rather frightening."

Me: "Not a problem but I am leaving in six weeks. I've already made arraignments at work for a week off and have reservations at a campground up there."

After sharing the dates and such Wynn promised to let me know shortly. As we walked out the door she asked about the non-fraternizing policy at work. I told her I would look into it.

Part 4

I asked our supervisor about the fraternizing policy the next Monday. The next day she got back to me and said it was a policy against management staff from messing with the other employees.

Janet: "Who do you plan on fucking or are you already?"

Me: "No one, I just heard about it the other day and was curious that's all."

Janet: "Liar."

Part 5

Wynn made arrangements for the week off telling Janet she and her mother were going to visit relatives in Ohio. We left Des Moines on a Sunday morning. Ten hours later we were settled into the campground. A couple of stops along the way, one for lunch and then to watch a big ship from Libya as it came into the harbor in Duluth. By mutual agreement we didn't do anything the first night. I confessed to being tired from the driving and Wynn was just happy to put off what was going to happen. After a great supper we sat outside and had a couple of beers until the mosquitoes drove us indoors. I guess I drink a lot of beer.

I sat up front while Wynn get ready for bed and when she hollered that it was my turn I moved to the back and joined her. Trying to keep her calm I turned my back to her and went to sleep. Sometime in the night I woke with a full bladder, damn beer. In seems I had moved in the night and I was spooning with Wynn. One hand was on her bare belly when her night shirt had rode up and my hard-on was snuggled in her butt crack. Carefully I moved back and crawled out of the bed and did my business. As I crawled back in I tried to keep away from her but as lay down with my back to her she rolled over and spooned me. As her breasts pushed against my back my pecker grew hard again. And when a hand rested on my shoulder I almost lost control.

As I went back to sleep I was making plans for the morning. Except it seemed Wynn had other plans. I woke up to her shaking me and telling me that breakfast was almost ready and I better get up if I wanted it warm. The smell of bacon and coffee convinced me that we could wait for the evening to do what I wanted to do.

There was no hiding the bulge in my boxers as I crawled out of the bed. I caught Wynn staring at it so as I stood up I made a big deal out of raising my arms, spreading my legs and stretching. As I told her how good I slept. She was all ready to go exploring, a baggy shirt, loose shorts that reached almost to her knees and boots already on. So I enjoyed a really great breakfast. But I did it in my boxers.

The day was great. Some many waterfalls and wonderful trails to follow that it was late before we made it back to the campground. Thank goodness for digital cameras. I must have taken several hundred photos. Wynn ran off to shower while I downloaded photos to my laptop and the backup drive. I was just finishing her photos when she came from the showers, telling me that by the time I had showered supper would be ready so I should get my buns in gear.

After we ate Wynn suggested we sit outside again for a bit. As we were drinking our beer she was yawning and saying how much we walked and how much she enjoyed it and how sore and tired she was. I was thinking she was trying to put off the next thing on the agenda.

Me: "Well maybe we should move back inside. It's getting dark and the bugs will be out shortly and I think it's time that we do something."

Wynn: "Ok...If that's what you think. I'm kind of sore but I wouldn't mind doing that fellatio and cunnilingus thing if you want. OK?"

Me: "Yup, that would be a good start, before we do something else."

We lay there kissing and touching as we slowly undressed each other. Wynn's body was all I pictured. Her long legs, firm body, tight butt and small upstanding tits were a sight to behold. And we did do that cunnilingus thing for a while. After I gave her a couple of orgasms it was time to try the other thing. She insisted on doing the fellatio thing first. Before I let her finish me that way I pulled back and told her it was time.

Me: "I'm only good for one shot these days and I don't want it to be this way. What you're doing is great but it's time to fuck."

Wynn: "Ok put your protection on and we can try it. But you promised to be gentle and take it slow right?"

Me: "I promise and no protection is needed. I had a vasectomy over twenty years ago. I have no desire to be a father."

I was slow and gentle. By the time I was completely in Wynn she was no longer afraid. In fact she turned into the tiger I thought might be hiding in her. She turned me every which way but loose. I expected it would be missionary style and that would be it. We tried a number of positions before I shot my load. Then she went back down on me and raised the dead for another round. It was the first time I had two orgasms in the same night in over ten years. Remarkable, and along the way Wynn had several more. It was midnight before we finally called it a night.

The next morning I woke up to her head on my stomach and warm breaths moving across the head of my pecker and fingers softly massaging my balls.

Wynn: "Want to do it again? Maybe one time you know, before breakfast ok? How about it big guy? If I had known it was so much fun I would have do it a whole lot earlier. How about it? Just one more time and then we can go out and check out a few more rivers."

It was almost noon before we were done and had breakfast. The campers across the road from us were watching us real close as we got ready to leave for the day. The guy gave me thumbs up as we pulled out of the campsite. I didn't realize that maybe we were a little noisy but something was clearly telling them a lot of activity was taking place.

That's how the week went. It was a little sex in the morning and then a great breakfast to start the day. We would hike and take photos and then stop for lunch at a local restaurant before going on to the next river. Then wonderful suppers, showers and then a lot of sex in the evenings, in fact we even stopped having a beer after supper most nights.

Wynn wasn't a big fan of swallowing my discharge so it was normally a prelude to the main event. But she was very talented with her mouth and tongue so she was able to get me hard a second time. I know it was just so she could get another trip down pleasure lane but I admit I was getting something out of it. I had more orgasms that week then maybe the previous three months.

As the week came to a close Wynn was almost finally satisfied.

Part 6

Wynn: "Wow. I don't believe how stupid I was. Intercourse, fucking is unbelievable. I have to admit I'm a little sore down there but if you can find a place to pull over before the Iowa state line I'm ready to go one more time. How about you big guy, and I do mean big. You got one more time in you? I can't believe I could take all that sausage you are packing down there. Wow oh baby! I'm a new woman."

All my previous thoughts about playing the field had disappeared. One short week with Wynn had turned the tables. I was seriously considering being a one woman man. I was not sure what love was but I may have found it. Then it crashed.

Wynn: "This was so much fun. I can't wait to try it out with others. I know that you're bigger than my Henry. You know, down there. How big is it? How long? Are you bigger than most? Or is my Henry maybe smaller than average? I'm going to have to check out other guys aren't I? Thank you John, you've opened my eyes to a whole new life. I can't wait. Thank you...Thank you. How can I ever repay you for your kindness and understanding? Oh...I could just kiss you."

The end

I hope this story meets with your approval. And gives you pause to think. Your comments and votes are appreciated.